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TeachMichigan – a statewide program funded by the Michigan legislature – seeks to increase teacher retention and improve teaching in districts serving high-poverty communities through two years of professional learning for participating educator “fellows.” However, professional development from an outside organization may not change educator practice across diverse local contexts. In this paper, we use interviews with 35 teachers to assess whether and how learning through TeachMichigan impacts teachers’ practice. Using complex systems theory, we examine intersections among teacher characteristics, school context, and professional learning activities to identify how these embedded systems shape teacher learning from external professional development and how teachers apply that learning in their local context. Findings have implications for supporting teacher professional learning at scale.